Beckmann rearrangement of cyclotriveratrylene (CTV) oxime: tandem Beckmann-electrophilic aromatic addition

The Beckmann rearrangement has been performed on the oxime of cyclotriveratrylene (CTV) with thionyl chloride affording the ring-expanded 10-membered ring amide exclusively in high yield. Modified conditions afford a helical pentacycle derived from an unusual tandem Beckmann rearrangement and electrophilic aromatic addition followed by demethylation and tautomerization. (c) 2008 Elsevier Ltd, All rights reserved,